CHI - SIN

$328 Find Cheap Flights from Chicago to Singapore

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 8/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Singapore.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Singapore.
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Cheap Flights from Chicago to Singapore (CHI-SIN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Singapore that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Singapore

Wed, Sep 24 - Tue, Sep 30
Cathay Pacific Logo
4:00 pm - 5:30 amORD-SIN
24h 30m1 stop
Cathay Pacific Logo
8:05 pm - 2:25 pmSIN-ORD
31h 20m1 stop
$622Cathay Pacific
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Tue, Aug 19 - Wed, Oct 22
Cathay Pacific Logo
4:00 pm - 5:30 amORD-SIN
24h 30m1 stop
Cathay Pacific Logo
8:05 pm - 2:25 pmSIN-ORD
31h 20m1 stop
$646Cathay Pacific
Find Deal
Mon, Nov 10 - Thu, Nov 27
United Airlines Logo
6:15 am - 8:15 pmORD-SIN
24h 00m1 stop
United Airlines Logo
10:20 pm - 6:02 amSIN-ORD
21h 42m1 stop
$658United Airlines
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Mon, Nov 10 - Mon, Nov 24
United Airlines Logo
7:10 am - 8:15 pmORD-SIN
23h 05m1 stop
United Airlines Logo
10:10 am - 10:59 pmSIN-ORD
26h 49m2 stops
$662United Airlines
Find Deal
Wed, Nov 12 - Mon, Nov 24
ANA Logo
7:10 am - 12:55 amORD-SIN
27h 45m2 stops
ANA Logo
10:20 pm - 7:20 amSIN-ORD
23h 00m1 stop
$707ANA
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Wed, Nov 12 - Tue, Nov 25
ANA Logo
7:10 am - 12:55 amORD-SIN
27h 45m2 stops
ANA Logo
6:35 am - 1:50 pmSIN-ORD
21h 15m1 stop
$710ANA
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Mon, Sep 1 - Wed, Sep 3
Delta Logo
9:30 am - 11:40 pmMDW-SIN
25h 10m2 stops
Delta Logo
1:10 am - 9:26 pmSIN-MDW
33h 16m2 stops
$1,139Delta
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Wed, Nov 12 - Tue, Nov 25
Delta Logo
5:59 pm - 12:10 amMDW-SIN
40h 11m2 stops
Delta Logo
1:30 am - 9:44 pmSIN-MDW
34h 14m2 stops
$1,144Delta
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Mon, Sep 1 - Wed, Sep 3
Korean Air Logo
9:30 am - 11:40 pmMDW-SIN
25h 10m2 stops
Korean Air Logo
1:10 am - 12:28 pmSIN-MDW
24h 18m2 stops
$1,485Korean Air
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Sun, Sep 21 - Sat, Sep 27
Korean Air Logo
9:20 am - 7:55 pmMDW-SIN
45h 35m2 stops
Korean Air Logo
7:30 am - 12:28 pmSIN-MDW
41h 58m2 stops
$1,942Korean Air
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Singapore?

What’s the cheapest day of the week to fly from Chicago to Singapore?

The average price of all round-trip flights from Chicago to Singapore clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Singapore, you should consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Thursdays.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Singapore is February, where tickets cost $877 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $1,799 and $1,428 respectively.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Singapore, you should book around 4 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$328
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 56% increase in price.
Flight from Chicago O'Hare Airport to Singapore

When to book flights from Chicago to Singapore

Are your dates flexible? Find out the best times to travel from Chicago to Singapore based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Singapore

  • Where is the yoga room at ORD?

    If you’d like to stretch as you wait for your flight to Singapore, you can visit O'Hare's yoga room located near the Urban Garden in the terminal 3 rotunda. Once you’re done with your practice, you can shower at the Hilton Athletic Club between terminal 2 and the parking garage. It’s worth noting that to access this club, you’ll part with some cash.

  • Does ORD have interesting destinations worth checking out?

    Yes, it does. While waiting for your flight to Singapore, you should check out the Urban Garden near the mezzanine level of the terminal 3 rotunda. The garden features over 26 plant varieties and is the perfect place to calm your nerves before a long flight.

  • Where can I get a wheelchair in SIN?

    Once you land at SIN, you can request a wheelchair at the airport’s customer service counters and information centers. Alternatively, to have a wheelchair waiting for you at the gate upon arrival, inform your airline at least 72 hours before the flight and they will make arrangements for you.

  • What are the layover options for flights from ORD to SIN?

    There are various layover destinations between Chicago and Singapore. San Francisco is one of the most preferred on this route. It mainly serves Singapore Airlines flights on the route. Incheon is another popular destination. It mainly serves Korean Airlines flights traveling from ORD to SIN.

  • What is the cheapest flight from Chicago to Singapore?

    In the last 3 days, the lowest price for a flight from Chicago to Singapore was $328 for a one-way ticket and $622 for a round-trip.

  • Do I need a passport to fly between Chicago and Singapore?

    Yes, you’ll need a passport to travel to Singapore from Chicago.

  • Which airports will I be using when flying from Chicago to Singapore?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Singapore Changi is the only airport in Singapore. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which aircraft models fly most regularly from Chicago to Singapore?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Singapore?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Singapore, with Star Alliance being the most commonly used for this route.

  • What is the most popular layover when flying to Singapore from Chicago?

    Hong Kong is the most popular layover city among KAYAK users traveling from Chicago to Singapore.

  • Which is the best airline for flights from Chicago to Singapore, Korean Air or ANA?

    The two airlines most popular with KAYAK users for flights from Chicago to Singapore are Korean Air and ANA. With an average price for the route of $1,279 and an overall rating of 8.4, Korean Air is the most popular choice. ANA is also a great choice for the route, with an average price of $1,571 and an overall rating of 8.4.

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Singapore from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Singapore with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Singapore?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Singapore from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Singapore

  • Chicago has two airports, O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW). All flights to Singapore leave from the O'Hare International Airport, which is the busier of the two airports. On your travel date, make sure to arrive at ORD at least 2 hours ahead of your departure time to give yourself enough time to get through the check-in and security lines.
  • When waiting for your flight to Singapore at ORD, you can enjoy relaxing beauty and spa services at XpresSpa. Located near gate M10 in terminal 5, this spa prides itself on having well-trained and adequately experienced professionals. It's the perfect way to relax before a long international flight.
  • If you need to charge your laptop or electronic devices, ORD has several power stations you can visit. In terminal 1 they are situated near gates B4, B12, B19, C15, and C28, while in terminal 2, they are situated near gates E8 and F2. Terminal 3’s power stations are near gates G9, H12, K12, and L10 and terminal 5’s are near gates M4, M7, and M13.
  • At Singapore Changi International Airport (SIN) there are various sculptures you can check out both before and after security in terminal 3. Make sure you stop by the world’s largest sculpture, the Kinetic Rain, in terminal 1. It's the perfect spot for a welcome-to-Singapore selfie!
  • If you would like to rent a car at SIN, you can easily do so at SIN's rental counters in the arrivals hall. There are several dependable car rental agencies to choose from like Avis, Budget, and Hertz. These car rental agencies are normally in operation from 7 am – 11 pm daily.

Reviews of the top 5 airlines serving from Chicago to Singapore

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Singapore. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Singapore? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.4
EVA AirOverall score based on 1224 reviews
8.3Comfort
8.6Crew
8.0Entertainment
8.1Food
8.4Boarding
Airline reviews

Very good service and food. Crew was professional and considerate. Cabin and restrooms were kept clean

10.0 ExcellentDale, Aug 2025SFO - TPE
Read more EVA Air reviews

Very good service and food. Crew was professional and considerate. Cabin and restrooms were kept clean

Flight Attendants could have been nicer and food portions could be bigger.

Great experience, comfort and food is delicious. Always great service and one time

The food from Los Angeles to Taipei made me throw up. The flight is also not comfort. But the staffs are very friendly and nice.

I have never heard of EVA air before but I am so happy my wife and I were able to flight on their planes twice. Everything on these flights just felt better than their competitors. As someone with longer legs any bit of extra leg spaces is appreciated. The different options for food and drinks were also a plus. They were extra careful to make sure my wife's eating restrictions were taken care for. They had a before take off and landing announcements on the built in tablets for each seat and it gave out information that was very helpful. Such as what and how to declare your items in the specific country you landed in, any odd items that may be illegal to bring it (and even the reasoning why) and any other information you might need to make your post flight experience better. Oh and the seats were more comfortable, had more ability to lean and the headrest was much better for flight sleeping. The only downside was there were "forced" ads on the tablet at take off for maybe 5-10 minutes but honestly, this flight was the cheapest option and had all the benefits listed above that is such an easy trade off. Im keeping an eye out for EVA air going forward.

I appreciate the email reminders for online check-in which made my entry to the lines less stressful. The flight was on schedule and on time. The baording staff were proactively helpful and approachable. The airplane inflight food, entertainment and comfies as well as provisions are excellent even in the economy seating. The airline transfer was smooth and easy! Luggage safe and intact! Thank you EVA airline for making my trip a reliable safe and comfortable experience.

Very smooth flight. Superb crew, great food and service. Slept most of the way. Excellent airline.

I was sleep when they brought the food. They had put a note on my seat. There was no food when I asked for food later. There was just one main meal served in this 14 hours flight. They offered me sandwich with ham which I don’t eat since I am pescatarian. Long story short I had to wait to get to TPE to get something to eat. I am extremely disappointed from the service. I have been flying EVA since I was 1 year old. Perhaps no more EVA for me. Seems EVA glorious day is long gone

Excellent food. Good service. Crammed Premium Economy seats. I Asked to change seats during check in. They told me the flight was fully booked. But on board I saw empty seats where I could have been easily relocated.

basic and only minimum of service, they offer nothing special

Check in process at the kiosk, crew in flight and overall comfort was good. Food selection could have been better. Flight from Hong Kong to Los Angeles did not have any vegetarian main course option, it was either sea food or chicken. Being a vegetarian I could only eat yogurt and fruit. Most international flights have one vegetarian main course dish which I found missing in Cathay Pacific menu.

Paid a premium a have a shorter transit time in Hong Kong, but Cathay pacific rebooked me and ended up waiting for 10 hrs in Hong Hong airport.

Entertainment for kids was good. Good was terrible, needs lots of work.

Better. I took an aisle seat this time. Although the overheard compartment above the seat ahead of me kept opening up during flight.

They ran out of food and were offering random food to passengers.

Flight was delayed at the last minute for six hours. Instead of delaying it to a normal hour, they moved it to 10 pm to essentially make it a redeye. There was no compensation or benefit offered for this inconvenience. Once on the plane, Inpaid for WiFi twice with both times it not working because of a “weak WiFi signal”, according to the flight attendants. They also chose the farther possible gates in both airports from the entrance/exit, even though they were one of the few active flights left so late in the evening. Overall it was pretty horrible.

I had high expectations but met with a below average experience. I hope the Airline will take a notice and improve.

I've stomach problems after 2 hours of flight, Iris, the flight purser not only did her best to make me feel comfortable, she went above and beyond providing pain relievers medicines and ointment. She look and found a doctor passenger on the flight to provide advise. She even report on ground staffs about my condition and provide wheelchair upon arrival. Kudos to her and Cathay Pacific!

Everything was fine and I have no complaints or things to note.

Overall, it was ok. However, the food was very sub-par.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Bough tickets with luggage, but made me pay at Airport as well

The economy seat was so uncomfortable, had not enough leg room for 13 hours flight, front seat basket was broken and couldn’t hold anything, food quality was horrible( we got food poisoned ) we charged for logged which used to be free. We paid too much for this flight and very disappointed. Turkish air line better to make satisfy and respect people instead of find different way to scam people.

This is really the rating of two flights. JFK to IST then IST to NQZ. New York to Istanbul was good. Good crew and all positives. The flight to Astana was so bad that brought it all down. Crew was nonexistent above the minimum, seats were cramped, and it was hot on the plane. Turkish Airlines seems to be slipping down to US based carriers level.

The 2 agents on the check in counter were super nice , helpful and very polite. Boarding was like a 1 2 3, I would recommend Turkish airlines for your next trip.

Everything was very good, except that the plane was an hour and a half late

flight with heavy turbulence old boeing 777 rest wasnt clean dashboard doesn’t work

Light and recline did not work on my seat. Very uncomfortable and could not read in the dark

Bad experience; they are not good anymore. They charge too much for luggage seat are so uncomfortable, Flight delays which may miss your next flight, they don’t care if you miss the flight or not. Zero customer services for front desk representatives Istanbul's airport I’m not using this airline any more.

I’ve been traveling for 20 years. I tried Turkish airline for the first time horrible horrible service and it would be my last time even if I get offer for a free ticket, I will not accept it. They have races and the worst Flight attendant

It wasn't good. I didn’t understand. They changed 320 dollars for 2 luggage. My ticket was regular and I paid almost 1200.00 dollars. Why they did charge? I want my money back.. thanks Yılmaz polat

They could care less about you. Just under a 4 hour delay in Seattle, leading into a missed connection in Vancouver, which led to 2 more delays that added up to 3 more hours leaving us to have to sleep on the floor of the Toronto airport cause they don't help you find accomodations and they just book you on the next flight out. Took an additional 14 hours to get home. Always given the brush off to get rid of us. Worst airline ever

All good but I could barely get my arms and legs into the room in front of me. Have never been so cramped before. Plane left the gate on time, taxied very quickly and took off without waiting. Unique. Arrival on time. No problem

Both flights are delayed so I rate the whole experience as mediocre.

I booked my flight months ago, and checked-in online about 12 hours before the flight. I received an email confirmation of check-in. I had no subsequent communication from Air Canada after my original booking. After arriving at the airport three hours before the flight, as instructed, I waited 90 minutes for an agent to appear to check my bag. I was informed that my flight had been canceled many weeks before, and that flight was no longer being run!! I showed a copy of my check-in confirmation, but no explanation could be found. I was placed on standby for the next flight and the connection. Luckily, those flights were not full and I arrived at my destination. I double checked my email, but I received no update about the flight from Air Canada until the day of the flight.

I had a good experience. I liked being informed about the status of my luggage

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

I was forcefully re-routed to another destination and was delayed a total of 8hours. I have still not received my bags, no one is taking responsibility. The agents at the airport lied to me that I will get to my destination same time as my previous flight where I was forcefully re-routed from.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

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